Top Chicago City Tours - page 5

4 Day Tour from Chicago: Detroit Toledo Buffalo and Niagara Falls

3.0

(1)

4 daysFree Cancellation

from $1,336

Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Chicago to Fashion Outlets of Chicago

5 hoursFree Cancellation

from $268

Comfortable Roundtrip Tour from your hotel in Chicago to Lighthouse Place Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Chicago to Lighthouse Place Outlets

6 to 7 hoursFree Cancellation

from $375

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Chicago to Chicago Premium Outlets

5 to 6 hoursFree Cancellation

from $295

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!

Chicago Private Tour

3 hoursFree Cancellation

from $300

Per group

Likely to Sell Out

Chicago Small Group City Tour

9 to 10 hoursFree Cancellation

from $415

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

Likely to Sell Out

Chicago-Milwaukee Small Group Tour

6 to 7 hoursFree Cancellation

from $415

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Art Institute of Chicago. Discover the awe-inspiring allure of Art Institute of Chicago, marvel at the grandeur of Chicago, and capture iconic moments and many more. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

Private Tour Art Institute of Chicago Guided Museum

5 hours

from $1,072

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience

Chicago Exotic Auto Experience

3 to 7 hours

from $1,800

Per group

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in the United States, Lake Superior, the largest freshwater lake in the world, and Lake Huron. Famous cities along the five great lakes: Chicago, Milwaukee and Traverse City along Lake Michigan, Green Bay along Green Bay, and Sault Ste. Mackinac Island, which was once selected as one of the top ten most beautiful islands in the world. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.

Chicago Milwaukee and Lakes 6 Day Tour

6 daysFree Cancellation

from $1,347

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Patricia_P, May 2026

Easily A Trip Highlight

This tour is easily a top highlight to our trip. It's worth the money since they do the work of planning out the route and have all the great info about each stop. Spencer was our guide and this tour hit all the marks - fun, educational, and memorable. Keep up the great work, Inside Chicago!

Chicago Crime and Mob Bus Tour

Kathleen_S, May 2026

Outstanding tour!

Very informative and entertaining. The guide provided nonstop, wide-ranging details while also keeping humor at the forefront. We stood in the alley where John Dillinger was gunned down, saw where the St. Valentine’s Day Massacre occurred, and visited a small museum dedicated to Chicago’s most notorious characters. Highly recommended!

Chicago City Minibus Tour

Karen_D, May 2026

Top notch!

Avery was so engaging, knowledgeable, and gave real inside into Chicago reality. Fascinating stories of the past, glorious and not so glorious. Buildings do have a life of their own and the buried stories they house are true tell alls of culture and history. Highly recommend this tour and Avery especially!

Chicago Favorites Ultimate Food and Walking Tour

Lawrence_C, Apr 2026

You’re Going to Want Jessika to Feed You

Chicago Favorites Ultimate Food and Walking Tour I now know why this Food & Walking Tour is called the Ultimate. How else could one person provide you with the four uniquely Chicagoan food items in just 2 hours. Jessica was bright, fun, energetic, and knowledgeable. We tried the Chicago-style pizza, popcorn, hot dog (NO KETCHUP), beef sandwich, and got dessert too. Fun time and a full meal. This is a great food tour, walking tour, and history lesson rolled-up into one tour. Highly recommended…especially when led by Jessika.

Chicago Architecture River Cruise

Carla_M, Apr 2026

Must do tour!

I did this tour last night with my husband and it was fantastic. I recommend going for the sunset option (for us this was around 6.45pm). The city architecture is stunning and our guide Sadie was phenomenal - funny, engaging and full of interesting information with a hint of dry wit! The ride was so smooth thanks to our captain and drink options were nice too. Definitely recommend! Be sure to layer up it gets real cold on the water!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Beth_B, Apr 2026

Beautiful view of Chicago at night

I went with my daughter and my 6 year old granddaughter to the 7:45 pm architectural boat tour and it did not disappoint! Between the beautiful view of the city at night and our tour guide John, we had a really nice time. Even my grand daughter enjoyed all the information. John was very entertaining and a wealth of information. When I come back to Chicago, I will be taking my husband.

Chicago in a Day: Food, History & Architecture Walking Tour

Jaydene_H, Apr 2026

A little bit of everything in one Chicago experience

We had a fantastic time on the Chicago architecture and food walking tour with our guide, Rich. Originally from New York and now proudly calling Chicago home, Rich brought great energy, knowledge, and personality to the experience. He shared fascinating facts about Chicago’s iconic architectural design along with interesting historical tidbits. One of my favorite stops was the Tribune Tower, where Rich explained how stones and artifacts from different states and countries were donated to represent their homelands. It was such a unique and memorable detail. The food portion of the tour was equally enjoyable, featuring classic Chicago favorites like Portillo's, Al's #1 Italian Beef, and Lou Malnati's Pizzeria. My personal favorite was the Chicago hot dog—it was delicious and a true local classic. Rich also did an excellent job keeping the group on schedule, even when it was challenging to find seating in the busy fast-food restaurants. His organization and dedication helped everything run smoothly. I highly recommend this tour to anyone wanting to experience the best of Chicago’s architecture, history, and food all in one outing!

Lake Michigan Sunset Cruise in Chicago

Marla_K, Apr 2026

Bring a blanket or warm...

Bring a blanket or warm jacket. It may look like a nice day out but on the water its chilly. Bring a backpack for water or a beverage and snack. Other then that we had a great time and it was nice to see the city all lit up. So beautiful and so relaxing. If your a drinker they have a full bar. They also have some snacks. Once out on the channel you can walk about the boat. Plenty of seating.

Chicago Architecture Center River Cruise aboard First Lady

Amy_A, Apr 2026

Outstanding Architecture Tour

Tour is extremely informative- volunteer docent was extremely knowledgeable and shared her knowledge in an entertaining manner. You can’t appreciate Chicago’s architecture until you see it from the water and learn the history. Money well spent and I will do this tour again!

Chicago Night Crimes Tour by Bus

Crystal_M, Oct 2025

Had an amazing time on...

Had an amazing time on this tour!!!! Hearing the stories and stoping at some of the same locations these gangsters and outlaws actually visited , stood, worked and even lost their lives at was quite the experience! The bus driver and tour guide were very professional . Our transportation bus was very nice, clean and comfortable. So glad I took this tour!! Thank you !!!